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Issue 9, 2010
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Design, synthesis, and self-assembly behavior of C3-symmetry discotic molecules via click chemistry

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Abstract

We prepared a series of C3-symmetry discogens with three 1,2,3-triazoles and a central benzene ring by a copper-catalyzed “click reaction” between 1,3,5-triethynylbenzene and 3,4,5-trialkoxybenzyl azides. According to the differential scanning calorimetry (DSC) data, compounds with octyl and dodecyl peripheries showed stable liquid crystalline (LC) phases at room temperature, and upon heating underwent an isotropization at 105.3 °C and 92.2 °C, respectively. Compound with octadecyl peripheries melted into a LC phase at 63.5 °C, and changed into a disordered liquid at 84.4 °C. As characterized by optical polarized microscopy (POM) and X-ray scattering techniques, all LC phases revealed hexagonally packed columns, the axes of which are aligned vertically on the glass substrate. Interestingly, the experimentally accessible crystalline phase of the compound with octadecyl chains kept the 2-D hexagonal columnar structure, although the interdisc distance within the columns changed at the transition from the LC to crystalline phase.

Graphical abstract: Design, synthesis, and self-assembly behavior of C3-symmetry discotic molecules via click chemistry

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Publication details

The article was received on 19 Oct 2009, accepted on 07 Dec 2009 and first published on 15 Jan 2010


Article type: Paper
DOI: 10.1039/B921685E
Citation: J. Mater. Chem., 2010,20, 1806-1810
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    Design, synthesis, and self-assembly behavior of C3-symmetry discotic molecules via click chemistry

    M. Ryu, J. Choi and B. Cho, J. Mater. Chem., 2010, 20, 1806
    DOI: 10.1039/B921685E

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